Canonical Smiles : C1C(C(C(C=C1C(=O)O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O
Inchi Key : QMPHZIPNNJOWQI-GDDAOPKQSA-N
IUPAC : (3R,4R,5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxycyclohexene-1-carboxylic acid
Pubchem ID : 5281762
Smiles : O=C(C=Cc1ccc(O)c(O)c1)OC1CC(C(=O)O)CC(=O)C1O
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PHYSICOCHEMICAL PROPERTIES
Molecular Weight : 336.08
Volume : 320.046
Density : 1.05
nHA : 8
nHD : 4
nRot : 5
nRing : 2
Max Ring : 6
nHet: 8
fChar : 0
nRig : 16
Flexibility : 0.312
Stereo Centers : 3
TPSA : 141.36
logS : -1.221
logP: 0.661
logD7.4 : 0.507
ABSORPTION
Caco-2 Permeability : -5.955
MDCK Permeability : 0.0000206399
Pgp-inhibitor : 0
Pgp-substrate : 0.158
HIA : 0.354
F20% : 0.043
F30% : 0.557
DISTRIBUTION
PPB : 0.766903
VD : 0.316
BBB Penetration : 0.35
Fu : 0.194534
METABOLISM
CYP 1A2 inhibitor : 0.027
CYP 1A2 substrate : 0.027
CYP 2C19 inhibitor : 0.038
CYP 2C19 substrate : 0.049
CYP 2C9 inhibitor : 0.022
CYP 2C9 substrate : 0.901
CYP 2D6 inhibitor : 0.008
CYP 2D6 substrate : 0.162
CYP 3A4 inhibitor : 0.022
CYP 3A4 substrate : 0.032
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MEDICINAL CHEMISTRY
QED : 0.353
SAscore : 3.714
Fsp : 0.312
MCE-18 : 52.143
NPscore : 1.683
Lipinski Rule : Accepted
Pfizer Rule : Accepted
GSK Rule : Accepted
Golden Triangle : Accepted
PAINS : 1
ALARM NMR Rule : 3
BMS Rule : 0
Chelator Rule : 1
TOXICOLOGY
hERG Blockers : 0.013
H-HT : 0.115
DILI : 0.078
AMES Toxicity : 0.013
Rat Oral Acute Toxicity : 0.172
FDAMDD : 0.043
Skin Sensitization : 0.139
Carcinogencity : 0.224
Eye Corrosion : 0.003
Eye Irritation : 0.038
Respiratory Toxicity : 0.07
Bioconcentration Factor : 0.257
IGC50 : 3.292
LC50FM : 4.184
LC50DM : 4.796
NR-AR : 0.463
NR-AR-LBD: 0.407
NR-AhR : 0.183
NR-Aromatase : 0.019
NR-ER : 0.252
NR-ER-LBD : 0.118
NR-PPAR-gamma : 0.679
SR-ARE : 0.185
SR-ATAD5 : 0.032
SR-HSE : 0.415
SR-MMP : 0.157
SR-p53 : 0.201
Acute/Aquatic Toxicity Rule : 5
Genotoxic Carcinogenicity Rule : 1
Non Genotoxic Carcinogenicity Rule : 1
Skin Sensitization Rule : 9
Non Biodegradable Rule : 2
SureChEMBL Rule : 0
FAF-Drugs4 Rule : 3
EXCRETION
CL : 13.624
t1/2 : 0.965
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